Triphenylphosphine → 3-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

HRID 391408

반응식

HRID 391408 반응식
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34]N1C(=O)CCC1=O>C(Cl)Cl>[Br:34][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

생성물 1

HCID 116013693-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

3-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile (0.33 mg, 1.64 mmol) and triphenylphosphine (0.86 g, 3.28 mmol) were combined in methylene chloride (6 mL) and cooled to 0° C. N-Bromosuccinimide (0.61 mg, 3.43 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with methylene chloride, washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.36 g (83%). 1H-NMR (CDCl3, 500 MHz) δ 7.97 (s, 2H), 7.84 (s, 1H), 4.50 (s, 2H).

후처리

  1. temperatureto warm to room temperature
  2. washwashed with concentrated sodium bicarbonate (2×), brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.36 g (83%)

출처 및 근거

ORD 기록
ord-7e23b24fbf744967ae3683bf41d8c9a8
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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